The ultimate issue facing the realization of maritime autonomous surface ships (MASS) is the need for unmanned operation to address questions of human recognition and judgment in ship operation that cannot be easily quantified. Therefore, the purpose of this study is to quantify the skills related ship operation, particularly skilled operator-level recognition of maneuvering environments and determination of ship maneuvers. Specifically, the utilization of behavioral and physiological data for quantitative evaluation is proposed. To do so, line-of-sight, cerebral blood flow, and heart rate fluctuations were selected as behavioral and physiological data. Simulator experiments were then conducted to analyze the relationship between the measured physiological data and the distance from other vessels, closest point of approach, time to closest point of approach, bearing rate, and so on.